


Always Watching (you)

by uhhargrove



Category: Stranger Things (TV 2016), Stranger Things - Fandom
Genre: After care, Anal, Bottom Jonathan Byers, F/M, Humiliation kink, MILF, Mommy Issues, Pegging, Spying, Top Karen Wheeler, degrading, handjobs, impact play (light), jerking off, maternal, pervert Jonathan
Language: English
Status: Completed
Published: 2020-01-07
Updated: 2020-01-07
Packaged: 2021-02-27 10:01:56
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,129
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22155214
Author URL: https://archiveofourown.org/users/uhhargrove/pseuds/uhhargrove
Summary: Jonathan gets caught snooping around Karen’s underwear drawer.
Relationships: Jonathan Byers/Karen Wheeler
Comments: 7
Kudos: 24





	Always Watching (you)

Jonathan Byers paused at the sound of his mother calling his name. He was in the midst of sweeping up the floors of Melvald’s General store in exchange for extra money for himself. Of course he had his other job, but that was mainly for helping his mom keep the house up and running and maybe afford a few classes at the community college. 

He leaned the broom up against a corner before making his way to where the smaller woman was crouching by a shelf, marking canned goods with price tag stickers. She was tired; it was obvious in the way her shoulders were slumped and how dark the bags under her eyes were growing. She worked long hours almost every day of the week to provide for her two sons, but with the lack of business as of late because of Starcourt being built, she just wasn’t making nearly as much money as she needed to.

“You uh, called me?,” Jonathan asked to get Joyce’s attention again.

“Yes, I need a favor.” Joyce stood up and walked over to the counter where two bags full of groceries sat, filled to the brim. 

“Karen needs a delivery. Something about having to drop Holly back off at school and she just needs someone to run them over for her really quick.”

“Oh, okay. Sure, I’ll do it.”

“Oh will you!,” Joyce sighed in relief and pulling him to her by the shoulders so she could lean up and kiss his cheek, “I really appreciate it.”

“No problem, mom.”

As Jonathan gathered the bags he couldn’t help but get a giddy feeling on the way to his car. Being alone in Karen Wheeler’s empty house was exciting enough. It was twice as big, maybe three times, as his own and everything there was just perfect. But aside from exterior and interior design, Jonathan was on edge because he had been suffering from an intense obsession with the mother of three.

He liked the way her hair fell, wishing he could reach out and touch the fluffy curls with his bare hands. He liked her sweet face that never held too much makeup. His eyes always took lasting glances of the older woman’s hips as she walked by, his skin always prickling at the sight of her ass swaying to and fro. Jonathan liked to tell himself he wasn’t a creep, liked to assure himself that he wasn’t borderline stalking this woman but it was hard to convince that to anyone else if he were to try. 

He knew there was no explanation grave enough to explain why he had spent a good deal of time in a red room developing pictures of the woman undressing. Low definition snapshots of the mother from her bedroom window were kept in a folder at the bottom of his underwear drawer and he tried to keep telling himself it was innocent. Harmless. 

It couldn’t be that bad to get off to the overexposed photos of the woman’s soft low-hanging breasts from time to time, could it?

Even when he was younger and more pubescent, going over to Karen’s house with his mother was almost like an enchanted wonderland. She’d always bake him and his brother cookies or let them watch cartoons on one of her huge television sets while she and his mom drank wine and laughed in the kitchen.

She always smelled so sweet, like warm blueberry muffins and baby powder, especially when she used to pull him in a secondary motherly hold, squishing his face into her cleavage and kissing his temple. It used to take him forever to push himself to wash the red lipstick off his ivory skin. He used to get jealous of Will getting to spend all of his time there with his best friend Mike, dreading the fact that Karen didn’t have any older sons to make excuses to hang out with.

Now that he was older, there was more and more reason for him to never step foot into this house unless if was to pick up his brother or visit Nancy from time to time, although they usually left the house as soon as he would get to the doorway. 

Jonathan parked his car into the Wheeler driveway, getting out and staring at the white home before him. He pulled the groceries out of the backseat, carrying them to the porch. He reached into the hanging potted plant by the doorbell, pulling out the spare key, the one Karen had told the Byers about a long time ago. Once he was inside, the smell of lavender-scented cleaning supplies engulfed him, chased by the light humming of the radio that sat on the fridge. 

Jonathan waste no time putting the cold items in the grocery list away before leaving the rest of the bags’ contents on the counter. He considered leaving then, he really did, but the urge to look around was even more inviting and with everyone out of the house it was positively harmless. After taking his shoes off at the door, he hurriedly climbed the steps of the three story home, two story if you didn’t count the basement.

His palms collected clammy sweat as he ascended to the upper portion of the home. He strolled past Nancy’s cotton-candy painted room, and past Mike’s darker room, then Holly’s bubbly kid room until he was standing in front of the master bedroom. He wipes his hands on the legs of his jeans before opening the barrier. It was such a high class setup, and every time he entered this room he was amazed at what having an abundance of money looked like. 

He wandered in, grazing his fingers against their soft duvet as he past. He was over at the dresser in seconds, sliding open the top drawer and getting a whiff of Karen’s sweet perfume that came with a kick at the end. He pushed through the soft bras, only pausing to cup one, imagining those tits were actually in front of him. At the bottom of the drawer was just what he was subconsciously looking for, a pair of Karen’s silky panties, this one in particular had a lacy waistband. 

He rubbed the material with his thumb before picking it up and holding them taut between both hands. He had planned to take one pair home with him as a reward to himself for being such a good helper and bring the groceries right over with no questions asked. He planned to put them right beside his folder or taboo Karen photos but the thought of that alone was enough to get his cock to stir in his jeans. 

He listened for sounds of cars or people in the house as he shakily slid his hand down to the front of his pants. His rough hand came to cup himself through his jeans, squeezing and pressing at his now growing bulge. Jonathan sighed softly as he began to unzip his fly, relieving ever present pressure as he released his cock from his confinements.

Jonathan Byers wasn’t big in the dick department, but he had enough length (when he was hard) to wrap his hand around himself and that was enough for him. Looking down at his angry red cock, Jonathan let a line of spit drop from his mouth down on his shaft, jerking himself off a few times to get himself completely out of his flaccid state and when he was fully hard he pumped small amount of Karen’s lotion into the seat of her panties before guiding them to his aching tip. Cupping the fabric in his hand just right, he slid himself into the cool lotion-coated pair of undies. 

He couldn’t help the soft gasp that left his parted lips as he started a slow sensual stroke. He couldn’t take his eyes off of the way the sexy pair of undergarments wrapped around him, rubbing the lotion into his cock. He wished he could freeze time and then stand there stroking himself but he knew eventually the woman would be home and she wouldn’t be very pleased. He wanted more than anything for this to be acceptable, for this to be normal. He wanted to touch himself while Karen instructed him how fast or how slow to do so. 

Jonathan tightened his grip, milking a few drops of precum out of his weighted balls. He bit his bottom lip and picked up the pace, only slowing every now and then when he felt he was about to blow his load too fast. 

“Oh..,” He moaned, “Oh god, Mrs. Wheeler.”

He closed his eyes and leaned his head back as he let a fantasy play behind his eyelids.

“You make me so hard, it’s horrible. I just can’t help myself,” he breathed and the sound of slickness met his ears. 

“Wanna cum for you...wanna cum in your panties like the sick freak I am,” and as the pressure was building for him to finally hit his peak, a throat was cleared.

Opening his eyes to see Karen standing before him was enough to make him jump but his dick was too far gone and he was cumming to his dismay. Shot after shot it didn’t seem to stop as he made eye contact with the woman, her arms crossed under her boobs.

He dropped the ruined pair of underwear, his mouth suddenly dry as he tried to speak and cover himself up at the same time.

“Muh-Mrs. Wheeler it’s not what it looked like I-,” he rambled in dumbfoundment as he struggled with his pants zipper.

Karen’s eyes were burning into him.

“Oh it’s not? So Jonathan Byers isn’t touching himself in my room right now, with my underwear might I add.”

Jonathan was turning red and trying to look everywhere but Karen’s face. His heart was hammering as she stepped closer to him.

“I should call your mother, or better yet I’ll just give a call to the station and let your step father know what you’ve been up to.”

Jonathan snapped his eyes back on her at the mention of Joyce and even worse, Hopper. He wouldn’t be able to sit right for weeks if that man got a hold of him for something like this.

“No, please! Mrs. Wheeler I’m sorry, I shouldn’t have done it. Just don’t call them. Make me clean for you or something else. Anything! Just don’t call my parents.”

Jonathan was close to crying almost as he pleaded to the honeyed blonde.

“Anything?”

“Yes, ma’am. Anything at all.”

Karen tapped her chin before nodding, “Sit on the bed and don’t move until I come back.”

Without another word, Karen left the room. Hesitantly, Jonathan made his way over to sit on the king size bed. It was a while before Karen returned and when she did, Jonathan was speechless to say the least. She was wearing nothing but a bra and the stockings that were under her work skirt. On top of that thin material was a dildo attached to some kind of harness to keep it on her crotch. 

Mrs. Wheeler was walking towards him basically naked, in heels, with a strap-on tightened to her pelvis. Jonathan felt his limp cock beginning to wake back up at the sight. However, that didn’t stop the embarrassed look crossing Jonathan’s face. Before he even went to speak, Karen was speaking.

“You ruined a pair of my favorite panties, Jonathan. It’s only fair I get to ruin you too. Unless you want out; calling your parents is still on the table.”

Jonathan quickly shook his head.

“Then you do as I say, Byers, understood?”

The boy began to rapidly nod at the woman.

“Good, now take off those jeans and get on your knees and suck me off. Come on let’s go.”

Once his jeans was discarded, dropping to his knees was easy when Karen was pulling him the whole way down. As soon as his knees hit the ground his chin was nudged up and he was met with the backside of the translucent red dildo and the illusion of Karen being so much taller than him. She tapped the cock on Jonathan’s face a few times with a small grin when he flinched at the light impact.

“You’re pathetic, you know that right. Getting yourself off in my room with my underwear, moaning my name. You know what that makes you look like?”

Karen held his chin, rubbing the silicon tip across his lips as he gave a breathy, “No, ma’am.”

“It makes you look like a horny slut, so open your mouth nice and wide for me slut.”

Jonathan obeyed, feeling Karen’s thumb pressing his tongue down so she could slide the dildo in his mouth. It was wider than he expected and when Karen moved her thumb, his lips were wrapped around it lewdly. 

“Hold your mouth just like that, we want my dick nice and wet so it’s easier to stretch you out, don’t we?” 

All Jonathan could do was hum around the toy, holding his mouth open as Karen softly fucked his mouth. The softness of this didn't last long before she was holding his head and thrusting into the back of his throat. She laughed as he gagged around her strap, even more amused with the fact that Jonathan was hard again.

“Oh what would your mother say if she knew what you were doing right now? How proud would she be of her perverted teenage boy being put in his place, drooling all over my pretty cock.”

Jonathan moaned as Karen pulled his hair, tugged his head back and sliding her cock out of his mouth. Saliva connected the boy’s mouth to Karen’s tip.

“Tell me how sorry you are for being such a horny pervert. I see the way you look at me.”

Jonathan took a moment to catch his breath before he spoke.

“I’m so sorry Mrs. Wheeler. It won’t happen again.”

Karen slapped him once across the cheek, making his head snap to the side. His stomach clenched at the impact as a small whine escaped his lips.

“you’re a fucking liar. You’re not sorry, and it will happen again. You want to know why, because you like this. You like being slapped around and told how disgusting you are.”

Karen nudged the boy away from her, “kiss my shoes and tell me what you really feel, huh. Go on and embarrass yourself some more, Byers.”

Jonathan looked up at her for a moment before dipping his head and placing a kiss on the toe of Karen’s heel. It was timid at first but then he began to kiss the shoes with earnest.

“Are you sorry, Byers?”

“No ma’am…,” a kiss to her shoe as he held himself up on shaky elbows.

“And why not?”

“Because I’m a pathetic horny pervert,” another kiss.

“What else?”

“I’m a slut…”

“That’s right, now turn around for me.”

Jonathan turned around, still on his hands and knees, gasping when Karen pushed his torso to the floor so that all that was in the air was his ass.

She leaned forward and spread his ass so she could see his puckered hole. She spat at the ring of muscles before rubbing it in. She slapped her cock between his cheeks and slid is back and forth on his hole. Jonathan was waiting with anticipation, almost holding his breath.

“You want me to fuck you?”

“Yes..Yes please.”

Karen started to push the tip, that was still coated with saliva, into the scrawny boy’s hole. Jonathan hissed in pain, letting the sound melt into a groan. Karen pushed her way in, enjoying how Jonathan just seemed to open up and take her.

“Fuck…,” he sighed into the carpet, the cock between his own legs feeling everpresent and heavy. 

“Look how well you’re taking me,” Karen said in awe, “the jocks at school must love you.”

She reached between his legs to massage the boy’s balls. He was so full of spunk it was painful. Karan brought her hand back, spitting into it before grabbing the boy by the dick again, pumping the shaft with a tight fist. Karen was thrusting while she jacked him off, making Jonathan rest his forehead onto the ground. He was moaning Karen’s name in pants, pushing back against her artificial cock while his sensitive dick was tugged. 

She used her free hand to grab onto on of his hips and slam their hips together, feeling accomplished when she hit that one spot inside of him that made his toes curl up. He was practicing shivering with pleasure as karen swirled her index finger over his leaking tip. Jonathan was bucking his hips at the feeling of slight overstimulation, not knowing whether he wanted to run from it or be given more of it. 

He could barely hold his ass up at this point, his thighs and knees were weakening with every deep thrust Karen gave to him. She let his cock go and grabbed both of his hips to make sure she could properly drill into the perverted twink good enough to drive a message.

“I can make you cum like this, Byers. Just like this, just from your tiny dick swinging back and forth from my thrusts. You’d like that wouldn’t you?” 

Karen was punctuating her sentences with deep snaps of her hips against his, blows that punched cries out of the teen. 

“Y-Yes, Mrs. Wheeler.”

“I want you to cum then, right now,” She kept her pace even as she reached up to pinch at his hard nipples. 

The wet sounds of her pounding his asshole left both of them hot and bothered and not shortly after, Jonathan came with a long drawn out moan. He was crying into the carpet as his dick gave up another powerful load of sex-driven cum, streams of it spilling onto the floor below them as his whole body seemed to spasm from the orgasm.

Karen pulled out of him, running her fingers gently through his sweat-soaked hair. She kissed his forehead just like she always did but it was different this time. He could feel the stickiness of the red lipstick on his temple, smiling softly. 

“Let’s get cleaned up before the family gets home, I’ll tell Joyce you’re helping me organize the fridge or something. I’ll run you a hot bath then run and get you a bottle of water, how’s that sound hun?”

She let Jonathan rest his face in her thighs. He nodded sleepily, “Can you bake cookies?”

“Sure thing, cutie...and next time, if you need me to milk those heavy balls of yours, just ask nicely.”

“Yes, ma’am.”

**Author's Note:**

> Sorry, I just needed a break from writing for my series, I have too many scenarios to write out that are in my head.


End file.
